Synlett 2014; 25(3): 355-358
DOI: 10.1055/s-0033-1340322
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© Georg Thieme Verlag Stuttgart · New York

Gram-Scale Synthesis of 3,5-Methanonipecotic Acid, a Nonchiral Bicyclic β-Amino Acid

Andriy V. Tymtsunik
a   Taras Shevchenko National University of Kyiv, Volodymyrska Street 64, Kyiv 01601, Ukraine   Fax: +380(44)5732643   eMail: gregor@univ.kiev.ua
b   Enamine Ltd., Alexandra Matrosova Street 23, Kyiv 01103, Ukraine
,
Vitaliy A. Bilenko
b   Enamine Ltd., Alexandra Matrosova Street 23, Kyiv 01103, Ukraine
,
Oleksandr O. Grygorenko*
a   Taras Shevchenko National University of Kyiv, Volodymyrska Street 64, Kyiv 01601, Ukraine   Fax: +380(44)5732643   eMail: gregor@univ.kiev.ua
,
Igor V. Komarov
a   Taras Shevchenko National University of Kyiv, Volodymyrska Street 64, Kyiv 01601, Ukraine   Fax: +380(44)5732643   eMail: gregor@univ.kiev.ua
b   Enamine Ltd., Alexandra Matrosova Street 23, Kyiv 01103, Ukraine
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Publikationsverlauf

Received: 21. September 2013

Accepted after revision: 06. November 2013

Publikationsdatum:
06. Dezember 2013 (online)


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Abstract

A scalable synthesis was developed of 3,5-methanoni­pecotic acid (3-azabicyclo[3.1.1]heptane-1-carboxylic acid), a rare example of a conformationally constrained nonchiral β-amino acid, potentially useful in peptide engineering and peptidomimetic drug design. A retrosynthetic strategy based on disconnections exclusively within the symmetry planes of the target and the intermediate molecules was found to be useful and might deliver expedite syntheses in other similar cases.

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